Book Your Academy Jumpstart Session with Dylan Stewart

Get personalized help navigating The MacWhisperer Academy, finding the resources that are right for you and creating a learning plan based on your Apple devices, questions and goals.

Choose a private one- or two-hour session with Dylan at this special introductory rate, available one time to new Academy members.

Start Your Academy Experience with Confidence

The Academy gives you access to live classes, recordings, SmartGuides, courses and an entire library of Apple education—but when you first join, it can be difficult to know where to begin.

Your Academy Jumpstart Session gives you focused, one-on-one time with Dylan to help you:

  • Understand everything included with your Academy membership
  • Learn how to navigate the Academy and find what you need
  • Identify the classes, recordings and SmartGuides most relevant to you
  • Create a personalized learning plan based on your devices and goals
  • Ask questions about how to get the most from your membership
  • Experience what it is like to work privately with Dylan

No searching through the Academy on your own. No wondering where to start. Just personal guidance designed to help you begin with clarity and confidence.

HOW IT WORKS

Step 1 - Choose Your Session 

Select either a one-hour or two-hour Academy Jumpstart Session.

One hour is ideal for an Academy orientation and personalized learning plan. Two hours gives you additional time to explore the Academy more deeply and begin addressing some of your Apple or technology questions with Dylan.

Step 2 - Complete Your Payment

Pay securely through our checkout. Once your purchase is complete, you’ll receive a confirmation email with your next steps.

Step 3 - Schedule & Get Reminders 

Choose the date and time that work best for you using our online scheduler. You’ll also receive automatic email and text reminders before your appointment.

Choose Your Academy Jumpstart Session

1-Hour Academy Jumpstart Session

Perfect for getting familiar with the Academy, understanding everything available to you and creating a personalized plan for where to begin.

What’s Included:

  • Private one-on-one time with Dylan
  • A guided tour of your Academy membership
  • Help finding the most relevant classes, recordings and SmartGuides
  • A personalized Academy learning plan
  • Answers to your membership and navigation questions
  • Follow-up notes by email

$150

Special New-Member Rate

Academy members normally receive private coaching with Dylan at the discounted member rate of $225 per hour. Dylan’s standard non-member coaching rate is $300 per hour.

This one-time Jumpstart offer gives new Academy members the opportunity to work privately with Dylan for just $150 per hour.


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2-Hour Academy Jumpstart Session

Ideal for members who want a complete Academy orientation along with additional time to begin working through their Apple devices, technology questions or personal learning goals.

What’s Included:

  • Extended one-on-one time with Dylan
  • A guided tour of your Academy membership
  • Help finding the most relevant classes, recordings and SmartGuides
  • A personalized Academy learning plan
  • Time to address additional Apple or technology questions
  • Follow-up notes by email

$300

Special New-Member Rate

Receive two private hours with Dylan for the same $150-per-hour introductory rate.

This is a one-time offer available exclusively to new Academy members.


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Your Digital Traveler Special Offer for a Limited Time!

Unlock the Full Power of Your Apple World — Month After Month

Join the MacWhisperer Academy for just $100/month and get the MacMasterclass (a $397 value) FREE!

This offer ends Monday, December 3 at midnight PT.

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Dylan's way of teaching is full of humor combined with such enthusiasm that it made learning the iPhone so enjoyable for me. By the end of each session I was enjoying using my iPhone more. I would never have found interest in the full range use of my phone without Dylan's class. the best the best the best the best the best the best 

STEVEN KIRALLA

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When I first found The MacWhisperer's classes I was pretty clueless about how to use my devices. Dylan walked me through my resistance to change with good humor and explained things in terms that made sense to me! I never thought I would get to this place, but I'm actually teaching the people around me how to use their devices now (at least I'd like to think so)!! Thank you!

TANYA RAGIR

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Before The MacWhisperer's Classes I was intimidated to use Siri or fully explore my phone's capabilities. But Dylan's class was empowering. His explanations are clear and concise and the pace is just right. You learn some really cool stuff. I bet most of the students didn't know what happens when you shake the iPhone vigorously. I certainly didn't.

THOMAS CLAFLIN

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Dylan's way of teaching is full of humor combined with such enthusiasm that it made learning the iPhone so enjoyable for me. By the end of each session I was enjoying using my iPhone more. I would never have found interest in the full range use of my phone without Dylan's class.

STEVEN KIRALLA

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When I first found The MacWhisperer's classes I was pretty clueless about how to use my devices. Dylan walked me through my resistance to change with good humor and explained things in terms that made sense to me! I never thought I would get to this place, but I'm actually teaching the people around me how to use their devices now (at least I'd like to think so)!! Thank you!

TANYA RAGIR

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Before The MacWhisperer's Classes I was intimidated to use Siri or fully explore my phone's capabilities. But Dylan's class was empowering. His explanations are clear and concise and the pace is just right. You learn some really cool stuff. I bet most of the students didn't know what happens when you shake the iPhone vigorously. I certainly didn't.

THOMAS CLAFLIN

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Make the Academy Work for You 

Everyone joins the Academy with different devices, experience levels and goals.

Some members want to better organize their photos. Others want to understand their iPhone, become more comfortable with their Mac, improve their digital security or finally learn the Apple features they know they have been missing.

During your Jumpstart Session, Dylan will help you identify what matters most to you and show you the best place to begin.

You won’t simply receive a tour of the Academy. You’ll leave with a practical learning path created specifically for you.

Ready to Jumpstart Your Academy Experience?

You’ve already taken the first step by joining The MacWhisperer Academy.

Now let Dylan help you understand everything available to you, identify the resources that fit your needs and create a personalized plan for moving forward.

You’ll also get to experience the difference that focused, one-on-one guidance can make.

Choose your one- or two-hour Jumpstart Session and schedule your private time with Dylan today.

Learn from Someone Who Makes Technology Feel Easy

Dylan Stewart has spent more than 20 years helping people understand their Apple devices and use technology with greater confidence.

His warm, practical teaching style makes complicated topics easier to understand—and easier to put into practice.

Your Academy Jumpstart Session brings that same teaching approach directly to you, focused entirely on your membership, devices and goals.

Get More from Your Academy Membership

You don’t have to figure out where to begin on your own.

Dylan will help you navigate the Academy, choose the right learning resources and build a path that makes sense for you.

This special new-member offer is available for a limited time and may only be purchased once.

Choose your session and reserve your time with Dylan today.

Choose your session